CN110003281B - Organometallic compound, organic light emitting device including the same, and diagnostic composition including the same - Google Patents
Organometallic compound, organic light emitting device including the same, and diagnostic composition including the same Download PDFInfo
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- CN110003281B CN110003281B CN201910007000.7A CN201910007000A CN110003281B CN 110003281 B CN110003281 B CN 110003281B CN 201910007000 A CN201910007000 A CN 201910007000A CN 110003281 B CN110003281 B CN 110003281B
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- 150000002902 organometallic compounds Chemical class 0.000 title claims abstract description 65
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- -1 sec-hexyl Chemical group 0.000 claims description 221
- 239000010410 layer Substances 0.000 claims description 141
- 229910052805 deuterium Inorganic materials 0.000 claims description 139
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 138
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 54
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 40
- 238000002347 injection Methods 0.000 claims description 39
- 239000007924 injection Substances 0.000 claims description 39
- 125000001624 naphthyl group Chemical group 0.000 claims description 39
- 230000005525 hole transport Effects 0.000 claims description 36
- 239000012044 organic layer Substances 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 230000000903 blocking effect Effects 0.000 claims description 23
- 239000004305 biphenyl Substances 0.000 claims description 20
- 235000010290 biphenyl Nutrition 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 239000000872 buffer Substances 0.000 claims description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 4
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- 150000001975 deuterium Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 66
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 37
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 26
- 239000000463 material Substances 0.000 description 25
- 125000006756 (C5-C30) carbocyclic group Chemical group 0.000 description 22
- 150000007857 hydrazones Chemical class 0.000 description 22
- 125000006753 (C1-C60) heteroaryl group Chemical group 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 125000003367 polycyclic group Chemical group 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 19
- 238000004440 column chromatography Methods 0.000 description 18
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 18
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 description 17
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 description 17
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 description 17
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 description 17
- 238000000151 deposition Methods 0.000 description 17
- 125000004076 pyridyl group Chemical group 0.000 description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 description 17
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 description 16
- 125000003943 azolyl group Chemical group 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 125000005561 phenanthryl group Chemical group 0.000 description 15
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 14
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 14
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 14
- 230000008021 deposition Effects 0.000 description 14
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 14
- 125000001725 pyrenyl group Chemical group 0.000 description 14
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 13
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 13
- 239000002019 doping agent Substances 0.000 description 13
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- 125000006754 (C2-C60) heteroarylalkyl group Chemical group 0.000 description 12
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 12
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 12
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 11
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 11
- 125000003373 pyrazinyl group Chemical group 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 10
- 125000002883 imidazolyl group Chemical group 0.000 description 10
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- 239000000126 substance Substances 0.000 description 10
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 9
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical group C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 238000001161 time-correlated single photon counting Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- H05B33/00—Electroluminescent light sources
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Abstract
Disclosed are organometallic compounds, organic light emitting devices including the same, and diagnostic compositions including the same. The organometallic compound is represented by formula 1, wherein, in formula 1, the groups and variables are the same as described in the specification. 1 (1)
Description
Cross reference to related applications
The present application claims priority of korean patent application No.10-2018-0001851 filed in the korean intellectual property office on 5 th 1 st 2018 and korean patent application No.10-2019-0000390 filed in 1 st 2019, and ownership rights generated therefrom, the contents of which are incorporated herein by reference in their entireties.
Technical Field
The present disclosure relates to organometallic compounds, organic light emitting devices including the organometallic compounds, and diagnostic compositions including the organometallic compounds.
Background
An Organic Light Emitting Device (OLED) is a self-emission device having improved characteristics in terms of viewing angle, response time, luminance, driving voltage, and response speed and producing a full color image.
In one example, an organic light emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emissive layer. The hole transport region may be disposed between the anode and the emission layer, and the electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons recombine in the emissive layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.
Meanwhile, luminescent compounds, such as phosphorescent compounds, may be used to monitor, sense, and detect biological materials such as various cells and proteins.
Various types of organic light emitting devices are known. However, there is still a need for OLEDs having low driving voltages, high efficiency, high brightness, and long lifetimes.
Disclosure of Invention
Organometallic compounds, organic light emitting devices comprising the organometallic compounds, and diagnostic compositions comprising the organometallic compounds are provided.
Additional aspects will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the provided embodiments.
According to an aspect of one embodiment, the organometallic compound is represented by formula 1:
1 (1)
In the formula (1) of the present invention,
M may Be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),
X 1 can be a bond, O, S, N (R '), P (R '), B (R '), C (R ') (R "), or Si (R ') (R"), and when X 1 is a bond, Y 1 can be directly bonded to M,
X 2-X4 may each independently be N or C, two selected from X 2-X4 may each be N, and the others may be C,
The bond between X 1 or Y 1 and M may be a covalent bond, one bond selected from the group consisting of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M may be a covalent bond, and the remaining two bonds may be coordination bonds,
Y 1 and Y 3-Y5 may each independently be C or N,
Among the pairs of X 2 and Y 3、X2 and Y 4、Y4 and Y 5、X51 and Y 3, and X 51 and Y 5, the components of each pair may be linked via chemical bonds,
The rings CY 1 through CY 5 may each be independently selected from a C 5-C30 carbocyclic group and a C 1-C30 heterocyclic group, and each of the rings CY 1, CY 3, and CY 4 may not be a benzimidazole group,
The ring metalated by ring CY 5, ring CY 2, ring CY 3, and M may be a6 membered ring,
X 51 can be selected from O、S、N-[(L7)b7-(R7)c7]、C(R7)(R8)、Si(R7)(R8)、Ge(R7)(R8)、C(＝O)、N、C(R7)、Si(R7)、 and Ge (R 7),
R 7 and R 8 may optionally be linked via a single bond, double bond, or a first linking group to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a,
T 1 and T 2 may each independently be a single bond, a double bond 、*-N(R9)-*'、*-B(R9)-*'、*-P(R9)-*'、*-C(R9)(R10)-*'、*-Si(R9)(R10)-*'、*-Ge(R9)(R10)-*'、*-S-*'、*-Se-*'、*-O-*'、*-C(＝O)-*'、*-S(＝O)-*'、*-S(＝O)2-*'、*-C(R9)＝*'、*＝C(R9)-*'、*-C(R9)＝C(R10)-*'、*-C(＝S)-*'、 or-c≡c',
L 1-L4 and L 7 may each be independently selected from a single bond, a substituted or unsubstituted C 5-C30 carbocyclic group, and a substituted or unsubstituted C 1-C30 heterocyclic group,
B1 to b4 and b7 may each independently be an integer of 1 to 5,
R 1-R4、R7-R10, R ', and R' may each independently be selected from hydrogen, deuterium, a deuterium-containing group, -F, -Cl, -Br, -I, -SF 5, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, substituted or unsubstituted C 1-C60 alkyl, substituted or unsubstituted C 2-C60 alkenyl, substituted or unsubstituted C 2-C60 alkynyl, substituted or unsubstituted C 1-C60 alkoxy, substituted or unsubstituted C 3-C10 cycloalkyl, substituted or unsubstituted C 1-C10 heterocycloalkyl, substituted or unsubstituted C 3-C10 cycloalkenyl, substituted or unsubstituted C 1-C10 heterocycloalkenyl, substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 7-C60 alkylaryl, substituted or unsubstituted C 6-C60 aryloxy, substituted or unsubstituted C 6-C60 arylthio, substituted or unsubstituted C 7-C60 aralkyl, substituted or unsubstituted C 1-C60 heteroaryl, 34unsubstituted C 2-C60 heteroaryl, substituted or unsubstituted C62 heteroaryloxy, substituted or unsubstituted C 3-C10 heteroaryl (=, substituted or unsubstituted C 7-C60 alkyl, substituted or unsubstituted C 7-C60 heteroaryl, substituted or unsubstituted C 7-C60 alkylthio, substituted or unsubstituted C 7-C60 alkylaryl, substituted or unsubstituted C5295 aryloxy, substituted or unsubstituted C5295 arylthio, substituted or unsubstituted C6269 heteroaryl (= (monovalent aromatic) and monovalent aromatic-substituted or unsubstituted C 2-C60 -polycyclic group,
C1 to c4 and c7 may each independently be integers from 1 to 5,
Z 1-Z4 can each independently be deuterium or a deuterium containing group,
A1-a4 and n1-n4 may each independently be an integer of 0-20,
I) When X 51 is O, S, C (=o), or N, the sum of N1 to N4 may be 1 or more, ii) when X 51 is N [ (L 7)b7-(R7)c7]、C(R7)、Si(R7), or Ge (R 7), a) R 7 may be deuterium or a deuterium-containing group; b) The sum of n1 to n4 may be 1 or more; or C) R 7 can be deuterium or a deuterium-containing group and the sum of n1 to n4 can be 1 or greater, and iii) when X 51 is C (R 7)(R8)、Si(R7)(R8), or Ge (R 7)(R8), a) at least one selected from R 7 and R 8 can be deuterium or a deuterium-containing group; b) The sum of n1 to n4 may be 1 or more; or c) at least one selected from R 7 and R 8 may be deuterium or a deuterium containing group and the sum of n1 to n4 may be 1 or more,
Two of the plurality of adjacent groups R 1 may optionally be linked to each other to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a,
Two of the plurality of adjacent groups R 2 may optionally be linked to each other to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a,
Two of the plurality of adjacent groups R 3 may optionally be linked to each other to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a,
Two of the plurality of adjacent groups R 4 may optionally be linked to each other to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a,
Two or more adjacent groups selected from R 1-R4、R7-R10, R ', and R' may optionally be joined to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a,
R 10a has the same definition as R 1,
At least one substituent of the substituted C 5-C30 carbocycle group, the substituted C 1-C30 heterocycle group, the substituted C 1-C60 alkyl group, the substituted C 2-C60 alkenyl group, the substituted C 2-C60 alkynyl group, the substituted C 1-C60 alkoxy group, the substituted C 3-C10 cycloalkyl group, the substituted C 1-C10 heterocycloalkyl group, the substituted C 3-C10 cycloalkenyl group, the substituted C 1-C10 heterocycloalkenyl group, the substituted C 6-C60 aryl group, the substituted C 7-C60 alkylaryl group, the substituted C 6-C60 aryloxy group, the substituted C 6-C60 arylthio group, the substituted C 7-C60 aralkyl group, the substituted C 1-C60 heteroaryl group, the substituted C 1-C60 heteroaryloxy group, the substituted C 1-C60 heteroarylthio group, the substituted C 2-C60 heteroarylalkyl group, the substituted C 2-C60 alkyl heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:
deuterium, -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, and C 1-C60 alkoxy;
C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, and C 1-C60 alkoxy each substituted with at least one selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 7-C60 alkylaryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroarylalkyl, C 2-C60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, -N (Q 11)(Q12)、-Si(Q13)(Q14)(Q15)、-B(Q16)(Q17), and-P (=o) (Q 18)(Q19);
C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 7-C60 alkylaryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroarylalkyl, C 2-C60 alkylheteroaryl, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 7-C60 alkylaryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroaralkyl, C 2-C60 alkylheteroaryl, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups, each of which is substituted with at least one member selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 7-C60 alkylaryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroarylalkyl, C 2-C60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, -N (Q 21)(Q22)、-Si(Q23)(Q24)(Q25)、-B(Q26)(Q27) and-P (=o) (Q 28)(Q29); and
-N (Q 31)(Q32)、-Si(Q33)(Q34)(Q35)、-B(Q36)(Q37), and-P (=o) (Q 38)(Q39);
Wherein Q 1-Q9、Q11-Q19、Q21-Q29, and Q 31-Q39 may each be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 1-C60 alkyl, C 1-C60 alkyl substituted with at least one selected from deuterium, C 1-C60 alkyl, and C 6-C60 aryl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 6-C60 aryl substituted with at least one selected from deuterium, C 1-C60 alkyl, and C 6-C60 aryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroarylalkyl, C 2-C60 alkylheteroaryl, a non-aromatic fused polycyclic group, and a monovalent non-fused polycyclic heteroaryl group.
According to an aspect of another embodiment, an organic light emitting device includes:
A first electrode;
a second electrode; and
An organic layer disposed between the first electrode and the second electrode,
Wherein the organic layer includes an emission layer and at least one organometallic compound represented by formula 1.
The organometallic compound in the organic layer may function as a dopant.
According to aspects of another embodiment, the diagnostic composition includes at least one organometallic compound represented by formula 1.
Drawings
These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments considered in connection with fig. 1, fig. 1 being a schematic cross-sectional view of an organic light-emitting device according to an embodiment.
Detailed Description
Reference will now be made in detail to the embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to the like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, the embodiments are described below only by referring to the drawings to illustrate aspects of the present description. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. The expression "at least one of the elements" when preceding or following a list of elements, for example, modifies the entire list of elements without modifying individual elements of the list.
It will be understood that when an element is referred to as being "on" another element, it can be directly on the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
It will be understood that, although the terms first, second, third, etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a first element, component, region, layer or section discussed below could be termed a second element, component, region, layer or section without departing from the teachings of the present embodiment.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
The term "or" means "and/or". It will be further understood that the terms "comprises" and/or "comprising," when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
Exemplary embodiments are described herein with reference to cross-sectional illustrations that are schematic illustrations of idealized embodiments. In this way, deviations from the shape of the figure as a result of, for example, manufacturing techniques and/or tolerances, will be expected. Thus, the embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, an area illustrated or described as flat may typically have rough and/or nonlinear features. Furthermore, the sharp corners illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the claims.
As used herein, "about" or "approximately" includes the stated values and is meant to be within an acceptable range of deviation from the particular values as determined by one of ordinary skill in the art in view of the measurements in question and the errors associated with the measurement of the particular quantities (i.e., limitations of the measurement system). For example, "about" may mean that the deviation from the stated value is within one or more standard deviations, or within ±30%, 20%, 10%, 5%.
In one embodiment, an organometallic compound represented by the following formula 1 is provided:
1 (1)
M in formula 1 may Be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).
In one embodiment, M may be Pt, pd, or Au, but embodiments of the present disclosure are not limited thereto.
X 1 in formula 1 can be a chemical bond (e.g., a covalent bond such as a single bond), O, S, N (R '), P (R '), B (R '), C (R ') (R "), or Si (R ') (R"). R 'and R' are the same as described above. When X 1 is a chemical bond, Y 1 and M may be directly connected to each other.
For example, X 1 may be O or S, but embodiments of the present disclosure are not limited thereto.
X 2-X4 in formula 1 may each independently be N or C, two selected from X 2-X4 may each be N, and the remainder may be C.
The bond between X 1 or Y 1 and M in formula 1 may be a covalent bond, one bond selected from the group consisting of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M may be a covalent bond, and the remaining two bonds may be coordination bonds. Thus, the organometallic compound represented by formula 1 may be electrically neutral.
In one or more embodiments, in formula 1,
I) X 2 and X 4 may each be N, X 3 may be C, the bond between X 2 and M and the bond between X 4 and M may each be a coordination bond, and the bond between X 3 and M may be a covalent bond, or
I) X 2 and X 3 may each be N, X 4 may be C, the bond between X 2 and M and the bond between X 3 and M may each be a coordination bond, and the bond between X 4 and M may be a covalent bond, or
Iii) X 3 and X 4 may be N, X 2 may be C, the bond between X 3 and M and the bond between X 4 and M may each be a coordinate bond, and the bond between X 2 and M may be a covalent bond, although embodiments of the present disclosure are not limited thereto.
In formula 1, Y 1 and Y 3-Y5 may each be independently C or N, and among the pairs of X 2 and Y 3、X2 and Y 4、Y4 and Y 5、X51 and Y 3, and X 51 and Y 5, the components in each pair may be connected via a chemical bond. Thus, the ring CY 5 in formula 1 may be a 5 membered ring fused to the ring CY 2.
The rings CY 1 to CY 5 in formula 1 may each be independently selected from a C 5-C30 carbocyclic group, and a C 1-C30 heterocyclic group, and each of the rings CY 1, CY 3, and CY 4 may not be a benzimidazole group.
For example, the rings CY 1 to CY 4 may each be independently selected from: i) A first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, and v) a fused ring in which one or more first rings and one or more second rings are fused to each other, wherein
The first ring may be selected from cyclopentane, cyclopentadiene, furan, thiophene, pyrrole groups a silol group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiophene group, a benzoxazole group,An azole group, i/>Azole groups,/>Diazole group, i/>Diazole group,/>Triazole group, i/>Triazole groups, thiazole groups, isothiazole groups, thiadiazole groups, isothiadiazole groups, thiatriazole groups, isothiatriazole groups, pyrazole groups, imidazole groups, triazole groups, tetrazole groups, azasilole groups, diazasilole groups, and triazasilole groups,
The second ring may be selected from adamantane groups, norbornane groups, norbornene groups, cyclohexane groups, cyclohexene groups, phenyl groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, and triazine groups, and
Each of the rings CY 1 to CY 4 may not be a benzimidazole group.
In one embodiment, the rings CY 1 through CY 4 can each be independently selected from the group consisting of a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo [9,10] phenanthrene group, a pyrene group,A group, a cyclopentadiene group, a1, 2,3, 4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a/(o)An azole group, i/>An azole group, a thiazole group, an isothiazole group,/>An diazole group, a thiadiazole group, a 5,6,7, 8-tetrahydroisoquinoline group, and a 5,6,7, 8-tetrahydroquinoline group, but embodiments of the present disclosure are not limited thereto.
The ring metalated ring formed by ring CY 5, ring CY 2, ring CY 3, and M in formula 1 may be a 6 membered ring.
In one embodiment, X 2 of ring CY 5, X 3 of ring CY 3, and X 4 of ring CY 4 in formula 1 may not constitute a carbene moiety. That is, regarding formula 1, 1) when X 2 is C, the bond between X 2 and M may be a covalent bond, 2) when X 3 is C, the bond between X 3 and M may be a covalent bond, and 3) when X 4 is C, the bond between X 4 and M may be a covalent bond.
With respect to formula 1, x 51 may be O、S、N-[(L7)b7-(R7)c7]、C(R7)(R8)、Si(R7)(R8)、Ge(R7)(R8)、C(＝O)、N、C(R7)、Si(R7)、 and Ge (R 7), and R 7 and R 8 may be optionally linked via a single bond, double bond, or first linking group to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a. Here, the C 5-C30 carbocyclic group and the C 1-C30 heterocyclic group may be understood by referring to the description about: i) The first ring, ii) the second ring, iii) the condensed ring in which two or more first rings are condensed with each other, iv) the condensed ring in which two or more second rings are condensed with each other, and v) the condensed ring in which one or more first rings and one or more second rings are condensed with each other, and R 10a can be understood by referring to the description about R 1, and L 7、b7、R7、R8, and c7 will be described in detail later.
The first linking group may be selected from *-O-*'、*-S-*'、*-C(R5)(R6)-*'、*-C(R5)＝*'、*＝C(R6)-*'、*-C(R5)＝C(R6)-*'、*-C(＝O)-*'、*-C(＝S)-*'、*-C≡C-*'、*-N(R5)-*'、 and-Si (R 5)(R6) -, and R 5 and R 6 are the same as described for R 1, and each represents a binding site to an adjacent atom.
In one or more embodiments, in formula 1,
I) Y 3-Y5 may each be C, the bond between X 51 and Y 3 and the bond between X 51 and Y 5 may each be a single bond, and X 51 may be O、S、N-[(L7)b7-(R7)c7]、C(R7)(R8)、Si(R7)(R8)、Ge(R7)(R8)、 or C (=o),
Ii) Y 3 and Y 4 may each be C, Y 5 may be N, the bond between X 51 and Y 3 may be a double bond, the bond between X 51 and Y 5 may be a single bond, and X 51 may be N, C (R 7)、Si(R7), or Ge (R 7),
Iii) Y 3 and Y 5 may each be C, Y 4 may be N, the bond between X 51 and Y 3 may be a single bond, the bond between X 51 and Y 5 may be a double bond, and X 51 may be N, C (R 7)、Si(R7), or Ge (R 7),
Iv) Y 3 can be N, Y 4 and Y 5 can each be C, the bond between X 51 and Y 3 can be a single bond, the bond between X 51 and Y 5 can be a double bond, and X 51 can be N, C (R 7)、Si(R7), or Ge (R 7), or
V) Y 3-Y5 may each be C, the bond between X 51 and Y 3 may be a double bond, the bond between X 51 and Y 5 may be a single bond, and X 51 may be N, C (R 7)、Si(R7), or Ge (R 7), but the embodiment is not limited thereto.
T 1 and T 2 in formula 1 may each independently be a single bond, a double bond 、*-N(R9)-*'、*-B(R9)-*'、*-P(R9)-*'、*-C(R9)(R10)-*'、*-Si(R9)(R10)-*'、*-Ge(R9)(R10)-*'、*-S-*'、*-Se-*'、*-O-*'、*-C(＝O)-*'、*-S(＝O)-*'、*-S(＝O)2-*'、*-C(R9)＝*'、*＝C(R9)-*'、*-C(R9)＝C(R10)-*'、*-C(＝S)-*'、 or-c≡c-, R 9 and R 10 may be linked optionally via a single bond, a double bond, or a second linking group to form a C 5-C30 carbocyclic group, unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group, unsubstituted or substituted with at least one R 10a. Here, the C 5-C30 carbocyclic group and the C 1-C30 heterocyclic group may be understood by referring to the description about: i) The first ring, ii) the second ring, iii) the fused ring in which two or more first rings are fused to each other, iv) the fused ring in which two or more second rings are fused to each other, and v) the fused ring in which one or more first rings and one or more second rings are fused to each other, and R 10a can be understood by reference to the description regarding R 1, and the second linking group can be understood by reference to the description regarding the first linking group.
In one embodiment, T 1 and T 2 in formula 1 may be single bonds, but the embodiment is not limited thereto.
L 1-L4 and L 7 in formula 1 may each be independently selected from a single bond, a substituted or unsubstituted C 5-C30 carbocyclic group, and a substituted or unsubstituted C 1-C30 heterocyclic group.
For example, L 1-L4 and L 7 in formula 1 may each be independently selected from:
A single bond, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo [9,10] phenanthrene group, a pyrene group, A group, a cyclopentadienyl group, a furan group, a thiophene group, a silole group, an indenyl group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group,/>An azole group, i/>An azole group, a thiazole group, an isothiazole group,/>Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo/>An azole group, a benzothiazole group, a benzo/>Diazole groups and benzothiadiazole groups; and
Each of which is substituted with at least one selected from the group consisting of a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo [9,10] phenanthrene group, a pyrene group,A group, a cyclopentadienyl group, a furan group, a thiophene group, a silole group, an indenyl group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group,/>An azole group, i/>An azole group, a thiazole group, an isothiazole group,/>Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo/>An azole group, a benzothiazole group, a benzo/>Diazole group and benzothiadiazole group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 1-C20 alkyl, C 1-C20 alkyl substituted with at least one deuterium, C 1-C20 alkoxy, phenyl substituted with at least one deuterium, biphenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, dimethyldibenzosilol, diphenyl dibenzosilol, -N (Q 31)(Q32)、-Si(Q33)(Q34)(Q35)、-B(Q36)(Q37), and-P (=o) (Q 38)(Q39);
Q 31-Q39 may each be independently selected from:
-CH3、-CD3、-CD2H、-CDH2、-CH2CH3、-CH2CD3、-CH2CD2H、-CH2CDH2、-CHDCH3、-CHDCD2H、-CHDCDH2、-CHDCD3、-CD2CH3、-CD2CD3、-CD2CD2H、 and-CD 2CDH2;
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl; and
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl each being substituted with at least one selected from the group consisting of: deuterium, C 1-C10 alkyl, and phenyl;
Embodiments of the present disclosure are not limited thereto.
B1 to b4 and b7 in formula 1 represent the numbers of L 1-L4 and L 7, respectively, and may each be independently an integer of 1 to 5. When b1 is 2 or more, two or more groups L 1 may be the same as or different from each other. b2-b4 and b7 may each be the same as described for b 1.
In one embodiment, L 1-L4 and L 7 in formula 1 may each be independently selected from:
a single bond; and
A phenyl group which is unsubstituted or substituted by at least one selected from the group consisting of: deuterium, -F, cyano, C 1-C20 alkyl, C 1-C20 alkyl substituted with at least one deuterium, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, dimethyldibenzosilol, and diphenyldibenzosilol substituted with at least one deuterium; and
B1 to b4 and b7 in formula 1 may be 1 or 2, but embodiments of the present disclosure are not limited thereto.
In one embodiment, b1-b4 and b7 in formula 1 may be 1 or 2, but embodiments of the present disclosure are not limited thereto.
R 1-R4、R7-R10, R', and R "may each be independently selected from hydrogen, deuterium, a deuterium-containing group, -F, -Cl, -Br, -I, -SF 5, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, substituted or unsubstituted C 1-C60 alkyl, substituted or unsubstituted C 2-C60 alkenyl, substituted or unsubstituted C 2-C60 alkynyl, substituted or unsubstituted C 1-C60 alkoxy, substituted or unsubstituted C 3-C10 cycloalkyl, substituted or unsubstituted C 1-C10 heterocycloalkyl, substituted or unsubstituted C 3-C10 cycloalkenyl, substituted or unsubstituted C 1-C10 heterocycloalkenyl, substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 7-C60 alkylaryl, substituted or unsubstituted C 6-C60 aryloxy, substituted or unsubstituted C 6-C60 arylthio, substituted or unsubstituted C 7-C60 aralkyl, substituted or unsubstituted C 1-C60 heteroaryl, substituted or unsubstituted C 2-C60 heteroaryloxy, substituted or unsubstituted C6762 heteroaryloxy, substituted or unsubstituted C3293 alkylaryl, substituted or unsubstituted C 7-C60 heteroaryl (=, substituted or unsubstituted C 7-C60 heteroaryl), substituted or unsubstituted C 7-C60 alkylthio, substituted or unsubstituted C 2-C60 heteroaryl (=, monovalent aromatic or unsubstituted heteroaryl (-Q). The deuterium containing group and Q 1-Q9 are the same as described above.
For example, R 1-R4、R7-R10, R', and R "may each be independently selected from:
hydrogen, deuterium, a deuterium-containing group, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, -SF 5、C1-C20 alkyl, and C 1-C20 alkoxy;
c 1-C20 alkyl and C 1-C20 alkoxy each substituted with at least one selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 1-C10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, and pyrimidinyl;
Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10] phenanthryl, pyrenyl, A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,/>Azolyl, isoOxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo/>Azolyl, isobenzo/>Azolyl, triazolyl, tetrazolyl,/>Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl;
Each being selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10] phenanthryl, pyrenyl, A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,/>Azolyl, i/>Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo/>Azolyl, isobenzo/>Azolyl, triazolyl, tetrazolyl,/>Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C 1-C20 alkyl, C 1-C20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10] phenanthryl, pyrenyl,/>, andA group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,/>Azolyl, i/>Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoAzolyl, isobenzo/>Azolyl, triazolyl, tetrazolyl,/>Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, and-Si (Q 33)(Q34)(Q35); and
-N (Q 1)(Q2)、-Si(Q3)(Q4)(Q5)、-B(Q6)(Q7), and-P (=o) (Q 8)(Q9);
here, Q 1-Q9 and Q 33-Q35 can be understood by referring to the description provided above.
In some embodiments, R 1-R4、R7-R10, R', and R "may each be independently selected from:
hydrogen, deuterium, a deuterium-containing group, -F, cyano, nitro, -SF 5, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, zhong Guiji, tert-decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [ 1.1.1.1 ] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.1.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, naphthyl, pyridinyl, benzofuranyl, and benzofuranyl;
methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, zhong Guiji, tert-decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, dibenzofluorenyl, dibenzothiophene, and dithienyl. Deuterium, -F, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, cyano, nitro, C 1-C10 alkyl, C 1-C10 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, and-Si (Q 33)(Q34)(Q35); and
-N (Q 1)(Q2)、-Si(Q3)(Q4)(Q5)、-B(Q6)(Q7), and-P (=o) (Q 8)(Q9);
Wherein Q 1-Q9 and Q 33-Q35 are the same as described above, but the embodiment is not limited thereto.
C1-c4 and c7 in formula 1 represent the number of R 1-R4 and R 7, respectively, and may each independently be an integer of 1-5 (e.g., 1,2, and 3). When c1 is 2 or more, two or more groups R 1 may be the same as or different from each other. c2-c4 and c7 can be understood by referring to the description with respect to c 1.
Z 1-Z4 in formula 1 may each independently be deuterium or a deuterium containing group.
For example, the deuterium containing group is a first group substituted with at least one deuterium, and the first group may be selected from the group consisting of substituted or unsubstituted C 1-C60 alkyl, substituted or unsubstituted C 2-C60 alkenyl, substituted or unsubstituted C 2-C60 alkynyl, substituted or unsubstituted C 1-C60 alkoxy, substituted or unsubstituted C 3-C10 cycloalkyl, substituted or unsubstituted C 1-C10 heterocycloalkyl, substituted or unsubstituted C 3-C10 cycloalkenyl, substituted or unsubstituted C 1-C10 heterocycloalkenyl, substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 7-C60 alkylaryl, substituted or unsubstituted C 6-C60 aryloxy, substituted or unsubstituted C 6-C60 arylthio, substituted or unsubstituted C 7-C60 aralkyl, substituted or unsubstituted C 1-C60 heteroaryl, substituted or unsubstituted C 1-C60 heteroaryloxy, substituted or unsubstituted C 1-C60 heteroarylthio, substituted or unsubstituted C 2-C60 heteroarylalkyl, substituted or unsubstituted C 2-C60 alkyl heteroaryl, substituted or unsubstituted monovalent aromatic or unsubstituted polycyclic aromatic, and unsubstituted monovalent heteroaromatic groups.
The term "deuterium containing group" as used herein refers to any group comprising at least one deuterium, which may be further substituted with substituents other than deuterium. The "deuterium containing group" is not "deuterium". For example, the term "deuterium-containing group" as used herein may include phenyl substituted with one deuterium, phenyl substituted with five deuterium and free of hydrogen (see formula 11-1), phenyl substituted with four deuterium and one tertiary butyl (see formulas 11-10 to 11-12), phenyl substituted with four deuterium and one-C (CD 3)3 and free of hydrogen (see formulas 11-7 to 11-9), -CDH 2、-CD3, etc. here, for example, the "phenyl substituted with one deuterium" refers to a deuterium-containing group in which the first group is "phenyl", and the "phenyl substituted with four deuterium and one tertiary butyl" refers to a deuterium-containing group in which the first group is "phenyl substituted with tertiary butyl".
In one embodiment, the deuterium containing group may be a first group substituted with at least one deuterium,
The first group may be selected from:
C 1-C20 alkyl and C 1-C20 alkoxy;
C 1-C20 alkyl and C 1-C20 alkoxy each substituted with at least one selected from the group consisting of: -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 1-C10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, and pyrimidinyl;
Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10] phenanthryl, pyrenyl, A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,/>Azolyl, isoOxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo/>Azolyl, isobenzo/>Azolyl, triazolyl, tetrazolyl,/>Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl;
Each being selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10] phenanthryl, pyrenyl, A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,/>Azolyl, i/>Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo/>Azolyl, isobenzo/>Azolyl, triazolyl, tetrazolyl,/>Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl: -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 1-C20 alkyl, C 1-C20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10] phenanthryl, pyrenyl,/>A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,/>Azolyl, i/>Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoAzolyl, isobenzo/>Azolyl, triazolyl, tetrazolyl,/>Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, and-Si (Q 33)(Q34)(Q35); and
-N (Q 1)(Q2)、-Si(Q3)(Q4)(Q5)、-B(Q6)(Q7), and-P (=o) (Q 8)(Q9);
here, Q 1-Q9 and Q 33-Q35 can be understood by referring to the description provided above.
In one embodiment, the deuterium containing group may be a first group substituted with at least one deuterium, and the first group may be selected from C 1-C20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, and terphenyl, each of which is unsubstituted or substituted with at least one selected from: -F, -CD 2H、-CDH2、-CF3、-CF2H、-CFH2, cyano, C 1-C10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, (C 1-C20 alkyl) phenyl, biphenyl, and terphenyl.
In one embodiment, the deuterium containing group i) may not include hydrogen or ii) may include at least one C 1-C10 alkyl group.
For example, in the deuterium containing group, all of the hydrogen of the "first group" is replaced with "deuterium", and thus, hydrogen is absent (e.g., such deuterium containing group may be selected from -CD3、-CD2(CD3)、-CD(CD3)2、-C(CD3)3、-CD2-C(CD3)3、-CD2-CD(CD3)2、-CD2-CD2(CD3)、-CD(CD3)-C(CD3)3、-CD(CD3)-CD(CD3)2、-CD(CD3)-CD2(CD3)、-C(CD3)2-C(CD3)3、-C(CD3)2-CD(CD3)2、-C(CD3)2-CD2(CD3)、 and formulas 11-1 to 11-9).
In some embodiments, the deuterium containing group can include at least one C 1-C10 alkyl group (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, sec-butyl, n-pentyl, isopentyl, t-pentyl, sec-pentyl, etc.), and such deuterium containing group can be, for example, one of formulas 11-10 to 11-12, although embodiments are not limited thereto.
In some embodiments, R 1-R4、R7-R10, R 'and R' may each be independently selected from hydrogen, deuterium, -F, cyano, nitro 、-SF5、-CH3、-CD3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2、-CD2(CD3)、-CD(CD3)2、-C(CD3)3、-CD2-C(CD3)3、-CD2-CD(CD3)2、-CD2-CD2(CD3)、-CD(CD3)-C(CD3)3、-CD(CD3)-CD(CD3)2、-CD(CD3)-CD2(CD3)、-C(CD3)2-C(CD3)3、-C(CD3)2-CD(CD3)2、-C(CD3)2-CD2(CD3)、, a group represented by formulas 9-1 to 9-19, a group represented by formulas 10-1 to 10-232, a group represented by formulas 11-1 to 11-41, and-Si (Q 1)(Q2)(Q3)(Q1-Q3 is the same as described above),
Z 1-Z4 may each independently be deuterium ,-CD3,-CD2H,-CDH2,-CD2(CD3),-CD(CD3)2,-C(CD3)3,-CD2-C(CD3)3,-CD2-CD(CD3)2,-CD2-CD2(CD3),-CD(CD3)-C(CD3)3,-CD(CD3)-CD(CD3)2,-CD(CD3)-CD2(CD3),-C(CD3)2-C(CD3)3,-C(CD3)2-CD(CD3)2,-C(CD3)2-CD2(CD3), and a group represented by one of formulas 9-14 to 9-19, 10-11, 10-12, and 11-1 to 11-41, but the embodiment is not limited thereto:
/>
/>
/>
/>
/>
With respect to formulas 9-1 to 9-19, 10-1 to 10-232, and 11-1 to 11-41, the binding sites to adjacent atoms are represented by, ph is phenyl, and TMS is trimethylsilyl.
In one or more embodiments, the deuterium containing group may be selected from -CD3、-CD2(CD3)、-CD(CD3)2、-C(CD3)3、-CD2-C(CD3)3、-CD2-CD(CD3)2、-CD2-CD2(CD3)、-CD(CD3)-C(CD3)3、-CD(CD3)-CD(CD3)2、-CD(CD3)-CD2(CD3)、-C(CD3)2-C(CD3)3、-C(CD3)2-CD(CD3)2、-C(CD3)2-CD2(CD3)、 and groups represented by one of formulas 11-1 to 11-41, but the embodiments are not limited thereto.
With respect to formula 1, a1-a4 represent the numbers of *-[(L1)b1-(R1)c1]、*-[(L2)b2-(R2)c2]、*-[(L3)b3-(R3)c3]、 and- [ (L 4)b4-(R4)c4 ] respectively, and n1-n4 represent the numbers of Z 1-Z4 respectively, and a1-a4 and n1-n4 may each independently be integers of 0-20.
In one or more embodiments, formula 1 may satisfy at least one of < condition a > to < condition D >:
< condition A >
N1 may be 1,2, 3 or 4.
< Condition B >
X 51 can be N [ (L 7)b7-(R7)c7 ] and R 7 can be deuterium or a deuterium containing group.
< Condition C >
N3 may be 1,2 or 3.
< Condition D >
N4 may be 1,2, 3 or 4.
In the formula (1) of the present invention,
I) When X 51 is O, S, C (=o), or N, the sum of N1 to N4 may be 1 or more,
Ii) when X 51 is N [ (L 7)b7-(R7)c7]、C(R7)、Si(R7), or Ge (R 7), a) R 7 is deuterium or a deuterium-containing group; b) The sum of n1 to n4 may be 1 or more; or c) R 7 is deuterium or a deuterium containing group and the sum of n1 to n4 may be 1 or more,
Iii) When X 51 is C (R 7)(R8)、Si(R7)(R8), or Ge (R 7)(R8), a) at least one selected from R 7 and R 8 can be deuterium or a deuterium-containing group; b) The sum of n1 to n4 may be 1 or more; or c) at least one selected from R 7 and R 8 may be deuterium or a deuterium containing group and the sum of n1 to n4 may be 1 or more.
That is, formula 1 may necessarily (substantially) comprise at least one deuterium and/or at least one deuterium containing group.
In one or more embodiments, in formula 1,
Y 3-Y5 can each be C and,
The bond between X 51 and Y 3 and the bond between X 51 and Y 5 may each be a single bond, and
A) X 51 can be O or S, and the sum of n1 to n4 can be 1, 2,3, or 4; b) X 51 can be N [ (L 7)b7-(R7)c7 ] and R 7 can be deuterium or a deuterium-containing group; c) X 51 can be N [ (L 7)b7-(R7)c7 ] and the sum of N1 to N4 can be 1, 2,3, or 4; d) X 51 can be N [ (L 7)b7-(R7)c7],R7 can be deuterium or a deuterium-containing group), and the sum of N1 to N4 can be 1, 2,3, or 4; e) X 51 can be C (R 7)(R8) and at least one selected from R 7 and R 8 can be deuterium or a deuterium containing group; or f) X 51 may be C (R 7)(R8), and the sum of n1 to n4 may be 1, 2,3, or 4, but the embodiment is not limited thereto.
In one or more embodiments, in formula 1,
I) n1=n2=n3=0, and n4 may be 1,2, 3, or 4,
Ii) n1=n2=n4=0, and n3 may be 1,2,3, or 4,
Iii) n1=n3=n4=0, and n2 may be 1,2, 3, or 4,
Iv) n2=n3=n4=0, and n1 may be 1,2, 3, or 4, or
V) n1=n2=n3=n4=0, x 51 can be N- [ (L 7)b7-(R7)c7]、C(R7)、Si(R7), or Ge (R 7), and R 7 can be deuterium or a deuterium-containing group; or alternatively
Vi) n1=n2=0, and n3 and n4 may each independently be 1,2, 3, or 4,
Vii) n1=n2=n3=0, N4 can be 1,2, 3, or 4, x 51 can be N- [ (L 7)b7-(R7)c7]、C(R7)、Si(R7), or Ge (R 7), and R 7 can be deuterium or a deuterium-containing group,
Viii) n1=n2=n4=0, N3 can be 1,2,3, or 4, x 51 can be N- [ (L 7)b7-(R7)c7]、C(R7)、Si(R7), or Ge (R 7), and R 7 can be deuterium or a deuterium-containing group, or
Ix) n2=n4=0, and n1 and n3 may each be independently 1,2, 3, or 4, but the embodiment is not limited thereto.
In one or more embodiments, with respect to formula 1,
I) X 1 can be a chemical bond and T 1 can be a single bond, formed byThe moiety represented may be a group represented by the formula CY1-B,
Ii) X 1 may be O, S, N (R '), P (R'), B (R '), C (R') (R "), or Si (R ') (R'), and T 1 may be a single bond, consisting ofThe moiety represented may be a group represented by the formula CY1-A, or
Iii) X 1 can be a bond, and T 1 can be *-N(R9)-*'、*-B(R9)-*'、*-P(R9)-*'、*-C(R9)(R10)-*'、*-Si(R9)(R10)-*'、*-Ge(R9)(R10)-*'、*-S-*'、*-Se-*'、*-O-*'、*-C(＝O)-*'、*-S(＝O)-*'、*-S(＝O)2-*'、*-C(R9)＝*'、*＝C(R9)-*'、*-C(R9)＝C(R10)-*'、*-C(＝S)-*'、 or-C≡C-, and is formed byThe moiety represented may be a group represented by formula CY 1-a:
With respect to formulas CY1-a and CY1-B, Y 1、CY1、L1、b1、R1、c1、a1、Z1, and N1 are the same as described above, Y 2 and Y 6 may each independently be N or C, and the bond between Y 1 and Y 2, the bond between Y 1 and Y 6, and the bond between Y 6 and Y 2 may each be a chemical bond.
In one or more embodiments, with respect to formula 1, the formula 1 is defined byThe moiety represented may be a group represented by one of formulas CY1-1 to CY 1-40:
/>
/>
In the formulae CY1-1 to CY1-40,
Y 1、R1、Z1, and n1 are the same as described above, and n1 may be an integer from 0 to 7,
X 19 can be C (R 19a)(R19b)、N[(L19)b19-(R19)c19), O, S, or Si (R 19a)(R19b),
L 19 may be the same as described for L 1;
b19 and c19 are the same as described for b1 and c1,
R 11-R19、R19a, and R 19b are the same as described for R 1.
A12 may be an integer from 0 to 2,
A13 may be an integer from 0 to 3,
A14 may be an integer from 0 to 4,
A15 may be an integer from 0 to 5,
A16 may be an integer from 0 to 6,
A17 may be an integer from 0 to 7,
* ' Represents a binding site to X 1 or M in formula 1, and
* Represents the binding site to T 1 in formula 1.
N1 in the formulae CY1-1 to CY1-40 has been described based on when n1 has its maximum value, and n1 may be an integer of 0 to 7, which varies depending on the corresponding chemical formula. For example, n1 in formula CY1-1 can be 0, 1,2, 3, or 4, n1 in formula CY1-2 can be 0, 1,2, or 3, and n1 in formula CY1-27 can be 0, 1,2, 3, 4, 5, 6, or 7.
In one or more embodiments, with respect to formula 1, the formula 1 is defined byThe moiety represented may be a group represented by one of formulas CY2-1 to CY 2-20: /(I)
In the formulae CY2-1 to CY2-20,
X 2、R2、Z2, and n2 are the same as described above, and n2 may be an integer from 0 to 3,
X 51 in the formulae CY2-1 to CY2-4 can be O、S、N-[(L7)b7-(R7)c7]、C(R7)(R8)、Si(R7)(R8)、Ge(R7)(R8)、 or C (=o),
X 51 in the formulae CY2-5 to CY2-20 can be N, C (R 7)、Si(R7), or Ge (R 7),
L 7、b7、R7 and c7 may be the same as described above,
A22 is an integer of 0 to 2,
A23 is an integer of 0 to 3,
* Represents a binding site to T 1 in formula 1,
* ' Represents a binding site to M in formula 1, and
* "Means a binding site to the cyclic CY 3 in formula 1.
N2 in the formulae CY2-1 to CY2-20 has been described based on when n2 has its maximum value, and n2 may be an integer of 0 to 3, which varies depending on the corresponding chemical formula. For example, n2 in formula CY2-1 can be 0, 1, 2, or 3, and n2 in formula CY2-2 can be 0, 1, or 2.
In one or more embodiments, with respect to formula 1, the formula 1 is defined byThe moiety represented may be a group represented by one of formulas CY3-1 to CY 3-12:
in the formulae CY3-1 to CY3-12,
X 3、R3、Z3, and n3 are the same as described above, and n3 may be an integer from 0 to 5,
X 39 can be C (R 39a)(R39b)、N[(L39)b39-(R39)c39), O, S, or Si (R 39a)(R39b),
L 39 may be the same as described with respect to L 3,
B39 and c39 may be the same as described for b3 and c3,
R 39a and R 39b may be the same as described for R 3,
A32 may be an integer from 0 to 2,
A33 may be an integer from 0 to 3,
A34 may be an integer from 0 to 4,
A35 may be an integer from 0 to 5,
* Represents a binding site to T 2 in formula 1,
* ' Represents a binding site to M in formula 1, and
* "Means a binding site to the cyclic CY 2 in formula 1.
N3 in the formulae CY3-1 to CY3-12 has been described based on when n3 has its maximum value, and n3 may be an integer of 0 to 5, which varies depending on the corresponding chemical formula. For example, n3 in formula CY3-1 can be 0, 1,2, or 3, and n3 in formula CY3-9 can be 0, 1,2,3, 4, or 5.
In one or more embodiments, with respect to formula 1, the formula 1 is defined byThe moiety represented may be a group represented by one of formulas CY4-1 to CY 4-26: /(I)
/>
In the formulae CY4-1 to CY4-26,
X 4、R4、Z4, and n4 can be the same as described above, and n4 can be 0,1,2,3,4,5, or 6,
X 49 can be C (R 49a)(R49b)、N[(L49)b49-(R49)c49), O, S, or Si (R 49a)(R49b),
L 49 may be the same as described with respect to L 4,
B49 and c49 are the same as described for b4 and c4,
R 41-R49、R49a, and R 49b are the same as described for R 4,
A42 may be an integer from 0 to 2,
A43 may be an integer from 0 to 3,
A44 may be an integer from 0 to 4,
A45 may be an integer from 0 to 5,
A46 may be an integer from 0 to 6,
* Represents the binding site to T 2 in formula 1, and
* ' Represents a binding site to M in formula 1.
N4 in the formulae CY4-1 to CY4-26 has been described based on when n4 has its maximum value, and n4 may be an integer of 0 to 6, which varies depending on the corresponding chemical formula. For example, n4 in formula CY4-1 can be 0, 1,2,3, or 4, n4 in formula CY4-2 can be 0, 1,2, or 3, and n4 in formula CY4-17 can be 0, 1,2,3, 4, 5, or 6.
In one or more embodiments, with respect to formula 1,
From the following componentsThe moiety represented may be a group represented by one of the formulae CY1 (1) to CY1 (16) and CY1-d (1) to CY1-d (18), and/or,/>
From the following componentsThe moiety represented may be a group represented by one of the formulae CY2 (1) to CY2 (20) and CY2-d (1) to CY2-d (15), and/or,
From the following componentsThe moiety represented may be a group represented by one of the formulae CY3 (1) to CY3 (12) and CY3-d (1) to CY3-d (13), and/or,
From the following componentsThe moiety represented may be a group represented by one of formulas CY4 (1) to CY4 (10) and CY4-d (1) to CY4-d (18), but the embodiment is not limited thereto. /(I)
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In the formulae CY1 (1) to CY1 (16), CY1-d (1) to CY1-d (18), CY2 (1) to CY2 (20), CY2-d (1) to CY2-d (15), CY3 (1) to CY3 (12), CY3-d (1) to CY3-d (13), CY4 (1) to CY4 (10), and CY4-d (1) to CY4-d (18),
X 2-X4、Y1、X51、R1-R4 and Z 1-Z4 may be the same as described above,
X 19 can be C (R 19a)(R19b)、N[(L19)b19-(R19)c19), O, S, or Si (R 19a)(R19b),
X 39 can be C (R 39a)(R39b)、N[(L39)b39-(R39)c39), O, S, or Si (R 39a)(R39b),
L 19、b19、R19 and c19 are the same as described for L 1、b1、R1 and c1 respectively,
L 39、b39、R39, and c39 are the same as described for L 3、b3、R3, and c3, respectively.
R 1a-R1d、R19a, and R 19b are the same as described for R 1,
R 3a-R3c、R39a, and R 39b are the same as described for R 3,
R 4a-R4d may be the same as described for R 4,
R 1-R4、R1a-R1d、R3a-R3c and R 4a-R4d are each other than hydrogen,
Z 1a-Z1d is the same as described for Z 1,
Z 3a-Z3c is the same as described for Z 3,
Z 4a-Z4d is the same as described for Z 4,
Regarding the formulae CY1 (1) to CY1 (16) and CY1-d (1) to CY1-d (18),' denotes a binding site to X 1 or M in formula 1, and X denotes a binding site to T 1 in formula 1,
Regarding the formulae CY2 (1) to CY2 (20) and CY2-d (1) to CY2-d (15), 'denotes a binding site to M in formula 1, denotes a binding site to T 1 in formula 1, and' denotes a binding site to a ring CY 3 in formula 1,
Regarding the formulae CY3 (1) to CY3 (12) and CY3-d (1) to CY3-d (13), ' represents a binding site to M in formula 1, ' represents a binding site to cyclic CY 2 in formula 1, and ' represents a binding site to T 2 in formula 1, and
Regarding the formulae CY4 (1) to CY4 (10) and CY4-d (1) to CY4-d (18),' denotes a binding site to M in formula 1, and x denotes a binding site to T 2 in formula 1.
In one embodiment, R 1-R4、R1a-R1d、R3a-R3c and R 4a-R4d in formulas CY1 (1) to CY1 (16), CY2 (1) to CY2 (20), CY3 (1) to CY3 (13), and CY4 (1) to CY4 (10) may each be other than deuterium and deuterium-containing groups.
In one or more embodiments, formula 1 may satisfy at least one of conditions 1 through 5:
Condition 1
In formula 1, the method consists ofThe moiety represented may be a group represented by one of the formulas CY1-d (1) to CY1-d (18).
Condition 2
In formula 1, the method consists ofThe moiety represented may be a group represented by one of the formulae CY2-d (1) to CY2-d (15).
Condition 3
In formula 1, the method consists ofThe moiety represented is a group represented by one of the formulae CY3-d (1) to CY3-d (13).
Condition 4
In formula 1, the method consists ofThe moiety represented may be a group represented by one of the formulas CY4-d (1) to CY4-d (18).
Condition 5
A) In formula 1, the method consists ofThe moiety represented may be a group represented by one of formulas CY2 (1) to CY2 (20), and b) with respect to formulas CY2 (1) to CY2 (20), i) X 51 is N- [ (L 7)b7-(R7)c7]、C(R7)、Si(R7), or Ge (R 7), and R 7 is deuterium or a deuterium-containing group, or ii) X 51 is C (R 7)(R8)、Si(R7)(R8), or Ge (R 7)(R8), and at least one of R 7 and R 8 is deuterium or a deuterium-containing group.
Regarding formula 1, i) two of the plurality of adjacent groups R 1 may optionally be linked to each other to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a, ii) two of the plurality of adjacent groups R 2 may optionally be linked to each other to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a, iii) two of the plurality of adjacent groups R 3 may optionally be linked to each other to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a, iv) two of the plurality of adjacent groups R 4 may optionally be linked to each other to form a C 5-C30 carbocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a, iii) two of the plurality of adjacent groups R 3 may be optionally linked to each other to form a C 1-C30 heterocyclic group that is unsubstituted or substituted with at least one R 10a, or a C 1-R4、R7-R10 heterocyclic group that is unsubstituted or substituted with at least one R3456. Here, the C 5-C30 carbocyclic group and the C 1-C30 heterocyclic group may be understood by referring to the description about: i) The first ring, ii) the second ring, iii) the fused ring in which two or more first rings are fused to each other, iv) the fused ring in which two or more second rings are fused to each other, and v) the fused ring in which one or more first rings and one or more second rings are fused to each other, and R 10a can be understood by referring to the description with respect to R 1.
"Azabenzothiophene, azabenzofuran, azaindene, azaindole, azabenzothiophene, azadibenzofuran, azafluorene, azacarbazole, and azadibenzosilole" may have the same skeletons as those of "benzothiophene, benzofuran, indene, indole, benzothiophene, dibenzofuran, fluorene, carbazole, and dibenzosilole", respectively, and may each be a heterocycle in which at least one of ring-forming carbon atoms is replaced with nitrogen.
In one embodiment, the organometallic compound represented by formula 1 may be represented by formula 1A as follows:
< 1A >
In formula 1A, the descriptions for M、X1-X4、Y1、X51、L1-L4、b1-b4、R1-R4、c1-c4、Z1-Z4、a1-a4 and n1-n4 may be the same as described in the present disclosure.
For example, the organometallic compound represented by formula 1 may be one of the following compounds 1 to 666, but embodiments of the present disclosure are not limited thereto.
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Z 1-Z4 in formula 1 may each independently be deuterium or a deuterium-containing group, and i) when X 51 is O, S, C (=o), or N, the sum of N1 to N4 may be 1 or more, ii) when X 51 is N [ (L 7)b7-(R7)c7]、C(R7)、Si(R7), or Ge (R 7), a) R 7 is deuterium or a deuterium-containing group; b) The sum of n1 to n4 may be 1 or more; or C) R 7 is deuterium or a deuterium-containing group and the sum of n1 to n4 is 1 or greater, and iii) when X 51 is C (R 7)(R8)、Si(R7)(R8), or Ge (R 7)(R8), a) at least one of R 7 and R 8 can be deuterium or a deuterium-containing group; b) The sum of n1 to n4 is 1 or more; or c) at least one of R 7 and R 8 is deuterium or a deuterium containing group and the sum of n1 to n4 is 1 or greater. That is, the organometallic compound represented by formula 1 may necessarily include at least one deuterium. Accordingly, the reduced mass (reducedmass) of the organometallic compound represented by formula 1 is changed, and thus, a molecular structure change by energy quenching due to vibration of the organometallic compound in an excited state is reduced. Due to the reduction of the change in the molecular structure, an electronic device including the organometallic compound represented by formula 1, for example, an organic light-emitting device including the organometallic compound represented by formula 1, may have improved lifetime characteristics.
In one or more embodiments, X 2-X4 in formula 1 may each independently be N or C, two selected from X 2-X4 may each be N, and the remaining one may be C, and the bond between X 1 or Y 1 and M may be a covalent bond, and one selected from the bond between X 2 and M, the bond between X 3 and M, and the bond between X 4 and M may be a covalent bond, and the remaining two bonds may each be a coordinate bond. In one embodiment, X 2 of ring CY 5, X 3 of ring CY 3, and X 4 of ring CY 4 in formula 1 may not constitute a carbene moiety. That is, regarding formula 1, 1) when X 2 is C, the bond between X 2 and M may be a covalent bond, 2) when X 3 is C, the bond between X 3 and M may be a covalent bond, and 3) when X 4 is C, the bond between X 4 and M may be a covalent bond. Accordingly, the structural change of the main emission portion of the organometallic compound represented by formula 1 in an excited state is reduced, and thus, the color purity of an electronic device including the organometallic compound, for example, an organic light-emitting device including the organometallic compound, can be improved.
In addition, each of the ring CY 1, the ring CY 3, and the ring CY 4 in formula 1 may not be a benzimidazole group. Accordingly, since steric hindrance of the ligand around the center metal M is improved, an electronic device including the organometallic compound, for example, an organic light-emitting device including the organometallic compound, can have improved lifetime characteristics and sharp electroluminescent peaks.
For example, the HOMO, LUMO, singlet (S 1) and triplet (T 1) energy levels of compounds 1 to 10 and 13 were evaluated by DFT methods using a Gaussian program (structurally optimized at the level of B3LYP,6-31G (d, p)). The evaluation results are shown in table 1 below.
TABLE 1
From table 1, it was confirmed that the organometallic compound represented by formula 1 has such electrical characteristics as to be suitable as a dopant for electronic devices such as organic light emitting devices.
The synthetic method of the organometallic compound represented by formula 1 can be recognized by one of ordinary skill in the art by referring to the synthetic examples provided below.
The organometallic compound represented by formula 1 is suitable for use in an organic layer of an organic light emitting device, for example, as a dopant in an emission layer of the organic layer. Accordingly, in another aspect, there is provided an organic light emitting device comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission layer and at least one organometallic compound represented by formula 1.
The organic light emitting device may have a low driving voltage, high efficiency, high power efficiency, high quantum efficiency, long lifetime, low roll-off ratio, and excellent color purity due to the inclusion of the organic layer including the organometallic compound represented by formula 1.
The organometallic compound of formula 1 can be used between an electrode pair of an organic light emitting device. For example, the organometallic compound represented by formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (i.e., the amount of organometallic compound represented by formula 1 is less than the amount of the host).
The expression "(organic layer) as used herein includes embodiments in which" (organic layer) includes the same organometallic compound represented by formula 1 "and embodiments in which" (organic layer) includes two or more different organometallic compounds represented by formula 1.
For example, the organic layer may include only compound 1 as the organometallic compound. In this regard, the compound 1 may be included in an emission layer of the organic light emitting device. In one or more embodiments, the organic layer may include compound 1 and compound 2 as the organometallic compound. In this regard, compound 1 and compound 2 may be included in the same layer (e.g., compound 1 and compound 2 may all be included in the emissive layer).
The first electrode may be an anode that is a hole injection electrode, and the second electrode may be a cathode that is an electron injection electrode; alternatively, the first electrode may be a cathode as an electron injection electrode and the second electrode may be an anode as a hole injection electrode.
In one embodiment, in the organic light emitting device, the first electrode is an anode and the second electrode is a cathode, and the organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
The term "organic layer" as used herein refers to a single layer and/or multiple layers disposed between a first electrode and a second electrode of an organic light emitting device. The "organic layer" may include, in addition to the organic compound, an organometallic complex including a metal.
Fig. 1 is a schematic view of an organic light emitting device 10 according to an embodiment. Hereinafter, a structure of an organic light emitting device according to an embodiment and a method of manufacturing the organic light emitting device according to an embodiment will be described with reference to fig. 1. The organic light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19 sequentially stacked.
A substrate may be additionally provided under the first electrode 11 or over the second electrode 19. For use as the substrate, any substrate used in a general organic light emitting device may be used, and the substrate may be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material used to form the first electrode 11 may be selected from materials having a high work function to promote hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).
The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO/Ag/ITO, but the structure of the first electrode 11 is not limited thereto.
An organic layer 15 is located on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in the stated order from the first electrode 11.
When the hole transport region includes a Hole Injection Layer (HIL), the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and/or langmuir-blodgett (LB) deposition.
When the hole injection layer is formed by vacuum deposition, deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100 to about 500 ℃, a vacuum pressure of about 10 -8 to about 10 -3 torr, and a deposition temperature of about 0.01 angstroms/secondSecond) -about/>Deposition rate per second. However, the deposition conditions are not limited thereto.
When the hole injection layer is formed using spin coating, coating conditions may vary depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 revolutions per minute (rpm) to about 5,000rpm, and the temperature at which the heat treatment to remove the solvent after coating may be about 80 ℃ to about 200 ℃. However, the coating conditions are not limited thereto.
The conditions for forming the hole transport layer and the electron blocking layer can be understood by referring to the conditions for forming the hole injection layer.
The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB, β -NPB, TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4',4″ -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-sulfostyrene) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-sulfostyrene) (PANI/PSS), a compound represented by the following formula 201, and a compound represented by the following formula 202:
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ar 101-Ar102 in formula 201 may each be independently selected from
Phenylene, pentalene, indenylene, naphthylene, azulenylene, heptylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthrylene, benzo [9,10] phenanthrylene, pyrenylene, andA group, a tetracene group, a picene group, a perylene group, and a pentacene group; and/>
Each of which is selected from at least one of substituted phenylene, pentalene, indenylene, naphthylene, azulenylene, heptylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthrylene, benzo [9,10] phenanthrylene, pyrenylene, andA group, a tetracene group, a picene group, a perylene group, and a pentacene group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, C 3-C10 cycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 1-C60 heteroaryl, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.
Xa and xb in formula 201 may each independently be an integer of 0 to 5, or 0, 1 or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.
R 101-R108、R111-R119 and R 121-R124 in formulas 201 and 202 may each be independently selected from:
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salts thereof, sulfonic acid or salts thereof, phosphoric acid or salts thereof, C 1-C10 alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C 1-C10 alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);
C 1-C10 alkyl or C 1-C10 alkoxy each substituted with at least one selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or salt thereof;
phenyl, naphthyl, anthracyl, fluorenyl, or pyrenyl; and
Phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl each substituted with at least one selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1-C10 alkyl, and C 1-C10 alkoxy,
Embodiments of the present disclosure are not limited thereto.
R 109 in formula 201 may be selected from:
phenyl, naphthyl, anthracyl, and pyridinyl; and
Phenyl, naphthyl, anthracenyl, and pyridinyl, each substituted with at least one selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 1-C20 alkyl, C 1-C20 alkoxy, phenyl, naphthyl, anthryl, and pyridyl.
According to one embodiment, the compound represented by formula 201 may be represented by formula 201A below, but embodiments of the present disclosure are not limited thereto:
201A
R 101、R111、R112, and R 109 in formula 201A can be understood by reference to the description provided herein.
For example, the compound represented by formula 201, and the compound represented by formula 202 may include, but are not limited to, the compounds HT1 to HT20 shown below:
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the hole transport region may have a thickness of about -About/>Such as about/>-AboutWithin a range of (2). When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the hole injection layer may have a thickness of about/>-About/>Such as about/>-About/>And the thickness of the hole transport layer may be within the range of about/>-About/>Such as about/>-About/>Within a range of (2). While not wanting to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in drive voltage.
In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.
The charge generating material may be, for example, a p-dopant. The p-dopant may be one selected from quinone derivatives, metal oxides, and cyano group-containing compounds, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinone dimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and cyano group-containing compounds such as the following compound HT-D1, but not limited thereto.
The hole transport region may include a buffer layer.
In addition, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.
Then, an emission layer (EML) may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the material used to form the emission layer.
Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from the materials for the hole transport region described above and a material for a host, which will be described later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be described later.
The emission layer may include a host and a dopant, and the dopant may include an organometallic compound represented by formula 1.
The host may include at least one selected from TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, and compound H51:
In one or more embodiments, the host may further include a compound represented by the following formula 301.
301
Ar 111 and Ar 112 in formula 301 may each be independently selected from:
Phenylene, naphthylene, phenanthrylene, and pyrenylene; and
Phenylene, naphthylene, phenanthrylene, and pyrenylene each substituted with at least one selected from the group consisting of: phenyl, naphthyl, and anthracenyl.
Ar 113-Ar116 in formula 301 may each be independently selected from:
C 1-C10 alkyl, phenyl, naphthyl, phenanthryl, and pyrenyl; and
Phenyl, naphthyl, phenanthryl, and pyrenyl, each substituted with at least one selected from the group consisting of: phenyl, naphthyl, and anthracenyl.
G, h, i, and j in formula 301 may each independently be an integer of 0 to 4, and may be, for example, 0, 1, or 2.
Ar 113 and Ar 116 in formula 301 may each be independently selected from
C 1-C10 alkyl substituted with at least one selected from phenyl, naphthyl, and anthracenyl;
phenyl, naphthyl, anthracyl, pyrenyl, phenanthryl, and fluorenyl;
Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, and fluorenyl each substituted with at least one selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, and fluorenyl; and
Embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the host can include a compound represented by the following formula 302:
302, a method of manufacturing a semiconductor device
Ar 122-Ar125 in formula 302 is the same as described in detail with respect to Ar 113 in formula 301.
Ar 126 and Ar 127 in formula 302 may each independently be C 1-C10 alkyl (e.g., methyl, ethyl, or propyl).
K and l in formula 302 may each independently be an integer from 0 to 4. For example, k and l may be 0, 1, or 2.
When the organic light emitting device is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, the emission layer may emit white light due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer.
When the emission layer includes a host and a dopant, the amount of the dopant may be in the range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
The thickness of the emissive layer may be in the range of about-About/>Such as about/>-About/>Within a range of (2). While not wanting to be bound by theory, it is understood that when the thickness of the emissive layer is within this range, excellent light emission characteristics can be obtained without a significant increase in the driving voltage.
Then, an electron transport region may be disposed on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single layer structure or a multi-layer structure including two or more different materials.
By referring to the conditions for forming the hole injection layer, the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include at least one of BCP, bphen, and BAlq, for example, but embodiments of the present disclosure are not limited thereto.
The hole blocking layer may have a thickness of about-About/>Such as about/>-About/>Within a range of (2). While not wanting to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a significant increase in drive voltage.
The electron transport layer may further include at least one selected from BCP, bphen, alq 3, BAlq, TAZ, and NTAZ.
In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but is not limited thereto:
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The electron transport layer may have a thickness of about -About/>Such as about/>-About/>Within a range of (2). While not wanting to be bound by theory, it is understood that when the thickness of the electron transport layer is within the ranges described above, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in drive voltage.
Further, the electron transport layer may further include a material including a metal in addition to the above-described materials.
The metal-containing material may include a Li complex. The Li complex may include, for example, the compound ET-D1 (lithium 8-hydroxyquinoline, liQ) or ET-D2.
The electron transport region may include an Electron Injection Layer (EIL) that facilitates electrons flowing therein from the second electrode 19.
The electron injection layer may include at least one selected from LiF, naCl, csF, li 2 O, and BaO.
The electron injection layer may have a thickness of about-About/>And e.g. about/>-About/>Within a range of (2). While not wanting to be bound by theory, it is understood that when the thickness of the electron injection layer is within the ranges described above, the electron injection layer may have satisfactory electron injection characteristics without a significant increase in drive voltage. /(I)
The second electrode 19 is located on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as a material for forming the second electrode 19. In order to manufacture a top emission type light emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinabove, the organic light emitting device has been described with reference to fig. 1, but embodiments of the present disclosure are not limited thereto.
Another aspect provides a diagnostic composition comprising at least one organometallic compound represented by formula 1.
The organometallic compound represented by formula 1 provides high luminous efficiency. Accordingly, the diagnostic composition including the organometallic compound can have high diagnostic efficiency.
The diagnostic compositions can be used in a variety of applications including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.
The term "C 1-C60 alkyl" as used herein refers to a straight or branched saturated aliphatic monovalent radical having from 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. The term "C 1-C60 alkylene" as used herein refers to a divalent group having the same structure as a C 1-C60 alkyl group.
The term "C 1-C60 alkoxy" as used herein refers to a monovalent group represented by-OA 101 (wherein a 101 is C 1-C60 alkyl), and examples include methoxy, ethoxy, and isopropoxy.
The term "C 2-C60 alkenyl" as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon double bond at the middle or end of a C 2-C60 alkyl group, and examples include ethenyl, propenyl, and butenyl. The term "C 2-C60 alkenylene" as used herein refers to a divalent group having the same structure as a C 2-C60 alkenyl group.
The term "C 2-C60 alkynyl" as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon triple bond at the middle or end of a C 2-C60 alkyl group, and examples include ethynyl, and propynyl. The term "C 2-C60 alkynylene" as used herein refers to a divalent group having the same structure as a C 2-C60 alkynyl group.
The term "C 3-C10 cycloalkyl" as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. The term "C 3-C10 cycloalkylene" as used herein refers to a divalent group having the same structure as a C 3-C10 cycloalkyl group.
The term "C 1-C10 heterocycloalkyl" as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, si and S as a ring-forming atom and having 1 to 10 carbon atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. The term "C 1-C10 heterocycloalkylene" as used herein refers to a divalent group having the same structure as a C 1-C10 heterocycloalkyl group.
The term "C 3-C10 cycloalkenyl" as used herein refers to a monovalent monocyclic group having 3-10 carbon atoms in its ring and having at least one carbon-carbon double bond and no aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C 3-C10 cycloalkenyl" as used herein refers to a divalent group having the same structure as the C 3-C10 cycloalkenyl.
The term "C 1-C10 heterocycloalkenyl" as used herein refers to a monovalent monocyclic group having in its ring at least one heteroatom selected from N, O, P, si, and S as ring forming atoms, 1-10 carbon atoms, and at least one double bond. Examples of C 1-C10 heterocycloalkenyl are 2, 3-dihydrofuryl and 2, 3-dihydrothienyl. The term "C 1-C10 heterocycloalkenylene" as used herein refers to a divalent group having the same structure as a C 1-C10 heterocycloalkenyl.
The term "C 6-C60 aryl" as used herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term "C 6-C60 arylene" as used herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Non-limiting examples of C 6-C60 aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, andA base. When the C 6-C60 aryl and C 6-C60 arylene each include two or more rings, the rings may be fused to each other. C 7-C60 alkylaryl refers to a C 6-C59 aryl substituted with at least one C 1-C54 alkyl.
The term "C 1-C60 heteroaryl" as used herein refers to a monovalent group having a heterocyclic aromatic system as follows: the heterocyclic aromatic system has at least one heteroatom selected from N, O, P, si, and S as a ring forming atom, and from 1 to 60 carbon atoms. The term "C 1-C60 heteroarylene" as used herein refers to a divalent group having a heterocyclic aromatic system as follows: the heterocyclic aromatic system has at least one heteroatom selected from N, O, P, si, and S as a ring forming atom, and from 1 to 60 carbon atoms. Examples of C 1-C60 heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When the C 1-C60 heteroaryl and C 1-C60 heteroarylene each include two or more rings, the rings may be fused to each other. C 2-C60 Alkylheteroaryl refers to C 1-C59 heteroaryl substituted with at least one C 1-C59 alkyl.
The term "C 6-C60 aryloxy" as used herein means-OA 102 (wherein a 102 is C 6-C60 aryl), the term "C 6-C60 arylthio" as used herein means-SA 103 (wherein a 103 is C 6-C60 aryl), and the term "C 7-C60 aralkyl" as used herein means-a 104A105 (wherein a 105 is C 6-C59 aryl and a 104 is C 1-C54 alkylene).
The term "C 1-C60 heteroaryloxy" as used herein refers to-OA 106 (wherein a 106 is C 1-C60 heteroaryl), the term "C 1-C60 heteroarylthio" as used herein means-SA 107 (wherein a 107 is C 1-C60 heteroaryl), and the term "C 2-C60 heteroarylalkyl" as used herein refers to-a 108A109(A109 is C 1-C59 heteroaryl, and a 108 is C 1-C59 alkylene.
The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) as follows: it has two or more rings condensed with each other, has only carbon atoms as ring-forming atoms, and has no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic groups include fluorenyl groups. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.
The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 2 to 60 carbon atoms) as follows: it has two or more rings condensed with each other, has a heteroatom selected from N, O, P, si, and S as a ring-forming atom in addition to a carbon atom, and has no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic groups include carbazolyl groups. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.
The term "C 5-C30 carbocyclic group" as used herein refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring forming atoms. The C 5-C30 carbocyclic group may be a monocyclic group or a polycyclic group.
The term "C 1-C30 heterocyclic group" as used herein refers to a saturated or unsaturated cyclic group having a heteroatom selected from N, O, si, P, and S as a ring-forming atom in addition to 1 to 30 carbon atoms. The C 1-C30 heterocyclic group may be a monocyclic group or a polycyclic group.
At least one of the substituents of the substituted C 5-C30 carbocyclic group, the substituted C 1-C30 heterocyclic group, the substituted C 1-C60 alkyl group, the substituted C 2-C60 alkenyl group, the substituted C 2-C60 alkynyl group, the substituted C 1-C60 alkoxy group, the substituted C 3-C10 cycloalkyl group, the substituted C 1-C10 heterocycloalkyl group, the substituted C 3-C10 cycloalkenyl group, the substituted C 1-C10 heterocycloalkenyl group, the substituted C 6-C60 aryl group, the substituted C 7-C60 alkylaryl group, the substituted C 6-C60 aryloxy group, the substituted C 6-C60 arylthio group, the substituted C 7-C60 aralkyl group, the substituted C 1-C60 heteroaryl group, the substituted C 1-C60 heteroaryloxy group, the substituted C 1-C60 heteroarylthio group, the substituted C 2-C60 heteroarylalkyl group, the substituted C 2-C60 alkyl heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from:
deuterium, -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, and C 1-C60 alkoxy;
C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, and C 1-C60 alkoxy each substituted with at least one selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 7-C60 alkylaryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroarylalkyl, C 2-C60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, -N (Q 11)(Q12)、-Si(Q13)(Q14)(Q15)、-B(Q16)(Q17), and-P (=o) (Q 18)(Q19);
C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 7-C60 alkylaryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroarylalkyl, C 2-C60 alkylheteroaryl, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
c 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 7-C60 alkylaryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroaralkyl, C 2-C60 alkylheteroaryl, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups, each of which is substituted with at least one member selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, -CD 3、-CD2H、-CDH2、-CF3、-CF2H、-CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C 1-C60 alkyl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 7-C60 alkylaryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroarylalkyl, C 2-C60 alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N (Q 21)(Q22)、-Si(Q23)(Q24)(Q25)、-B(Q26)(Q27), and-P (=o) (Q 28)(Q29); and
-N (Q 31)(Q32)、-Si(Q33)(Q34)(Q35)、-B(Q36)(Q37), and-P (=o) (Q 38)(Q39);
Wherein Q 11-Q19、Q21-Q29, and Q 31-Q39 may each be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 1-C60 alkyl, C 1-C60 alkyl substituted with at least one selected from deuterium, C 1-C60 alkyl, and C 6-C60 aryl, C 2-C60 alkenyl, C 2-C60 alkynyl, C 1-C60 alkoxy, C 3-C10 cycloalkyl, C 1-C10 heterocycloalkyl, C 3-C10 cycloalkenyl, C 1-C10 heterocycloalkenyl, C 6-C60 aryl, C 6-C60 aryl substituted with at least one selected from deuterium, C 1-C60 alkyl, and C 6-C60 aryl, C 6-C60 aryloxy, C 6-C60 arylthio, C 7-C60 aralkyl, C 1-C60 heteroaryl, C 1-C60 heteroaryloxy, C 1-C60 heteroarylthio, C 2-C60 heteroarylalkyl, C 2-C60 alkylheteroaryl, a non-aromatic fused polycyclic group, and a monovalent non-fused polycyclic heteroaryl group.
Hereinafter, the compound and the organic light emitting device according to the embodiment are described in detail with reference to synthesis examples and examples. However, the organic light emitting device is not limited thereto. The expression "using B instead of a" used in describing the synthesis examples means that the amount of a used is the same as the amount of B used in terms of molar equivalents.
Examples
Synthesis example 1: synthesis of Compound 3
Synthesis of intermediate 3-C
2G (g) (6.60 mmol) of starting material 3-A, 2.53g (7.26 mmol,1.1 eq., equiv.) of starting material 3-B, 0.53g (0.46 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0)), and 2.74g (19.79 mmol,3 eq.) of potassium carbonate were mixed with a 48ml mixture comprising Tetrahydrofuran (THF) and H 2 O in a volume ratio of 3:1, and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature, and the precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with Ethyl Acetate (EA)/H 2 O, and purified by column chromatography to obtain 1.7g (78% yield) of intermediate 3-C. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝444.28(M+H)+
Synthesis of Compound 3
1.5G (3.37 mmol) of intermediate 3-C and 1.68g (4.05 mmol,1.2 eq.) of K 2PtCl4 are mixed with a mixture comprising 80ml of AcOH (acetic acid) and 4ml of H 2 O, and the mixture is refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with Methylene Chloride (MC) and washed with H 2 O, and purified by column chromatography to obtain 1.1g (yield 51%) of compound 3. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝637.23(M+H)+
Synthesis example 2: synthesis of Compound 17
Synthesis of intermediate 17-C
2G (4.19 mmol) of starting material 17-A, 1.93g (4.61 mmol,1.1 eq.) of starting material 17-B, 0.34g (0.29 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0), and 1.74g (12.57 mmol,3 eq.) of potassium carbonate were mixed with a 30ml mixture comprising THF and H 2 O in a 3:1 volume ratio and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature, and the precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with EA/H 2 O and purified by column chromatography to obtain 1.9g (66% yield) of intermediate 17-C. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝688.42(M+H)+
Synthesis of Compound 17
1.8G (2.61 mmol) of intermediate 17-C and 1.3g (3.14 mmol,1.2 eq.) of K 2PtCl4 were mixed with a mixture comprising 65ml of AcOH and 3ml of H 2 O and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with MC and washed with H 2 O, and purified by column chromatography to obtain 1.41g (61% yield) of compound 17. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝881.37(M+H)+
Synthesis example 3: synthesis of Compound 24
Synthesis of intermediate 24-C
2G (3.75 mmol) of starting material 24-A, 1.73g (4.12 mmol,1.1 eq.) of starting material 24-B, 0.30g (0.26 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0), and 1.82g (11.25 mmol,3 eq.) of potassium carbonate were mixed with 27ml of a mixture comprising THF and H 2 O in a 3:1 volume ratio and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature, and the precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with EA/H 2 O and purified by column chromatography to obtain 1.9g (yield 68%) of intermediate 24-C. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝744.48(M+H)+
Synthesis of Compound 24
1.7G (2.28 mmol) of intermediate 24-C and 1.3g (3.14 mmol,1.2 eq.) of K 2PtCl4 were mixed with a mixture comprising 57ml of AcOH and 3ml of H 2 O and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with MC and washed with H 2 O, and purified by column chromatography to obtain 1.41g (65% yield) of compound 24. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝937.43(M+H)+
Synthesis example 4: synthesis of Compound 27
Synthesis of intermediate 27-C
2G (3.39 mmol) of starting material 27-A, 1.84g (3.73 mmol,1.1 eq.) of starting material 27-B, 0.27g (0.24 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0), and 1.41g (10.18 mmol,3 eq.) of potassium carbonate were mixed with 27ml of a mixture comprising THF and H 2 O in a volume ratio of 3:1, and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature, and the precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with EA/H 2 O and purified by column chromatography to obtain 2.2g (yield of 74%) of intermediate 27-C. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝875.57(M+H)+
Synthesis of Compound 27
1.5G (1.71 mmol) of intermediate 27-C and 0.85g (3.14 mmol,1.2 eq.) of K 2PtCl4 are mixed with a mixture comprising 43ml of AcOH and 2ml of H 2 O and the resulting mixture is refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with MC and washed with H 2 O, and purified by column chromatography to obtain 1.1g (60% yield) of compound 27. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝1068.52(M+H)+
Synthesis example 5: synthesis of Compound 31
Synthesis of intermediate 31-C
2G (3.58 mmol) of starting material 31-A, 1.65g (3.73 mmol,1.1 eq.) of starting material 31-B, 0.29g (0.25 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0), and 1.48g (10.74 mmol,3 eq.) of potassium carbonate were mixed with 26ml of a mixture comprising THF and H 2 O in a 3:1 volume ratio and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature, and the precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with EA/H 2 O and purified by column chromatography to obtain 1.8g (yield of 65%) of intermediate 31-C. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝769.48(M+H)+
Synthesis of Compound 31
1.7G (2.21 mmol) of intermediate 31-C and 1.1g (2.65 mmol,1.2 eq.) of K 2PtCl4 are mixed with a mixture comprising 55ml of AcOH and 3ml of H 2 O and the resulting mixture is refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with MC and washed with H 2 O, and purified by column chromatography to obtain 1.2g (56% yield) of compound 31. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝962.43(M+H)+
Synthesis example 6 Synthesis of Compound 99
Synthesis of intermediate 99-C
2G (3.28 mmol) of starting material 99-A, 1.52g (3.61 mmol,1.1 eq.) of starting material 99-B, 0.27g (0.23 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0), and 1.36g (9.84 mmol,3 eq.) of potassium carbonate were mixed with 36mL of a mixture comprising THF and H 2 O in a 3:1 ratio, and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature, and then, a precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with EA/H 2 O and subjected to column chromatography to complete the manufacture of 2.1g (78% yield) of intermediate 99-C. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝824.54(M+H)+
Synthesis of Compound 99
2G (2.42 mmol) of intermediate 99-C and 1.21g (2.91 mmol,1.2 eq.) of K 2PtCl4 are mixed with a mixture comprising 61mL of AcOH and 3mL of H 2 O and the resulting mixture is refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with MC and washed with H 2 O, and subjected to column chromatography to complete the production of 1.3g (53% yield) of compound 99. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝1017.49(M+H)+
Synthesis example 7 Synthesis of Compound 157
Synthesis of intermediate 157-C
2G (3.5 mmol) of starting material 157-A, 1.64g (3.85 mmol,1.1 eq.) of starting material 157-B, 0.28g (0.24 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0), and 1.45g (10.50 mmol,3 eq.) of potassium carbonate were mixed with a 38mL mixture comprising THF and H 2 O in a 3:1 ratio, and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature, and then, a precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with EA/H 2 O and subjected to column chromatography to complete the production of 2.1g (76% yield) of intermediate 157-C. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝791.55(M+H)+
Synthesis of Compound 157
2G (2.52 mmol) of intermediate 157-C, 1.26g (3.03 mmol,1.2 eq.) of K 2PtCl4 are mixed with a mixture comprising 63mL of AcOH and 3mL of H 2 O and the resulting mixture is refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with MC and washed with H 2 O, and subjected to column chromatography to complete the production of 1.2g (48% yield) of compound 157. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝984.50(M+H)+
Synthesis example 8 Synthesis of Compound 186
Synthesis of intermediate 186-C
2G (3.61 mmol) of starting material 186-A, 1.73g (3.97 mmol,1.1 eq.) of starting material 186-B, 0.29g (0.25 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0), and 1.50g (10.84 mmol,3 eq.) of potassium carbonate were mixed with a mixture comprising THF and H 2 O in a 3:1 ratio, and the resulting mixture was refluxed overnight. The obtained resultant was cooled to room temperature, and then, a precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with EA/H 2 O and subjected to column chromatography to complete the manufacture of intermediate 186-C in 1.8g (64% yield). The obtained compound was confirmed by LC-MS.
LC-MS m/z＝780.48(M+H)+
Synthesis of Compound 186
1.5G (1.92 mmol) of intermediate 186-C and 0.96g (2.3 mmol,1.2 eq.) of K 2PtCl4 are mixed with a mixture comprising 48mL of AcOH and 3mL of H 2 O and the resulting mixture is refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with MC and washed with H 2 O, and subjected to column chromatography to complete the production of 0.8g (43% yield) of compound 186. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝973.43(M+H)+
Synthesis example 9 Synthesis of Compound 448
Synthesis of intermediate 448-C
2G (3.51 mmol) of starting material 448-A, 1.89g (3.86 mmol,1.1 eq.) of starting material 448-B, 0.28g (0.25 mmol,0.07 eq.) of tetrakis (triphenylphosphine) palladium (0), and 1.45g (10.52 mmol,3 eq.) of potassium carbonate were mixed with a 38mL mixture comprising THF and H 2 O in a 3:1 ratio, and the resultant was refluxed overnight. The obtained resultant was cooled to room temperature, and then, a precipitate was removed therefrom to obtain a filtrate. The filtrate was washed with EA/H 2 O and subjected to column chromatography to complete the production of 2.0g (73% yield) of intermediate 448-C. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝852.48(M+H)+
Synthesis of Compound 448
1.8G (2.11 mmol) of intermediate 448-C and 1.05g (2.53 mmol,1.2 eq.) of K 2PtCl4 are mixed with a mixture comprising 53mL of AcOH and 3mL of H 2 O and the resulting mixture is refluxed overnight. The obtained resultant was cooled to room temperature and filtered to obtain a precipitate, which was then mixed with MC and washed with H 2 O, and subjected to column chromatography to complete the production of 1.1g (50% yield) of compound 448. The obtained compound was confirmed by LC-MS.
LC-MS m/z＝1045.43(M+H)+
Evaluation example 1: evaluation of photoluminescence Quantum yield (PLQY)
A solution of PMMA in CH 2Cl2, 5 weight% (wt%) CBP, and compound 3 were mixed, and the resultant was coated on a quartz substrate by using a spin coater, and then, heat-treated in an oven at a temperature of 80 ℃ and cooled to room temperature to obtain a film.
The PLQY of compound 3 in the film was evaluated by using Hamamatsu Photonics absolute PL quantum yield measurement system equipped with a xenon lamp light source, monochromator, photon multichannel analyzer, and integrating sphere and using PLQY measurement software (Hamamatsu Photonics, ltd., shizuoka, japan), and the same experiment was performed on each of compounds 17, 24, 27, and 31. The results are shown in Table 2.
TABLE 2
| Numbering of compounds | PLQY |
| 3 | 0.978 |
| 17 | 0.999 |
| 24 | 0.998 |
| 27 | 0.999 |
| 31 | 0.999 |
| 99 | 0.993 |
| 157 | 0.986 |
| 186 | 0.999 |
| 448 | 0.985 |
From table 2, it was confirmed that compounds 3, 17, 24, 27, 31, 99, 157, 186 and 448 had high PLQY (in the film).
Evaluation example 2: decay time measurement
A quartz substrate washed with chloroform and pure water was prepared, and then, predetermined materials shown in table 3 were vacuum co-deposited under a vacuum of 10 -7 torr to prepare films 1 to 9 having a thickness of 50 nanometers (nm).
TABLE 3 Table 3
| Film name | Compounds for use in membrane manufacture |
| Film 1 | CBP Compound 3 (9:1 by weight) |
| Film 2 | CBP Compound 17 (9:1 by weight) |
| Film 3 | CBP Compound 24 (9:1 weight ratio) |
| Film 4 | CBP Compound 27 (9:1 weight ratio) |
| Film 5 | CBP Compound 31 (9:1 by weight) |
| Film 6 | CBP Compound 99 (9:1 weight ratio) |
| Film 7 | CBP Compound 157 (9:1 by weight) |
| Film 8 | CBP Compound 186 (9:1 by weight) |
| Film 9 | CBP Compound 448 (9:1 by weight) |
The Photoluminescence (PL) spectra of each of films 1 to 9 were measured at room temperature by using FluoTime as a TRPL measurement system manufactured by PicoQuant inc. And PLS340 (excitation wavelength=340 nm, spectral width=20 nm) as a pump source of PicoQuant inc. Then, the main peak of each spectrum was determined, and the number of photons emitted at the wavelength of the photon pulse (pulse width=500 picoseconds) applied by PLS340 to each of films 1 to 9 was repeatedly measured over time based on time-dependent single photon count (TCSPC), thereby obtaining a TRPL curve that was sufficient for fitting. The obtained results were fitted with two or more decay functions to obtain T Attenuation of (Ex), i.e. the decay time of each of the membranes 1 to 9. The results obtained therefrom are shown in table 4. The function used for fitting is as shown in equation 1, and from among the T Attenuation of values obtained from the respective exponential decay functions used for fitting, the largest T Attenuation of is obtained as T Attenuation of (Ex). In this regard, the same measurement is made in the dark state (where the pump signal into the film is blocked) for the same measurement time as that used to obtain the TRPL curve to obtain a background signal curve or baseline for use as a baseline for fitting.
Equation 1
TABLE 4 Table 4
From table 4, it was confirmed that compounds 3, 17, 24, 27, 31, 99, 157, 186 and 448 have excellent decay time characteristics.
Example 1
The ITO glass substrate was cut into dimensions of 50mm×50mm×0.5mm (mm=millimeter), then sonicated in acetone, isopropyl alcohol, and pure water for 15 minutes each, and then cleaned by exposure to UV ozone for 30 minutes.
Then, the m-MTDATA was measured at 1 angstrom/sec @Deposition rate per second) on an ITO electrode (anode) of the glass substrate to form a thin film having a deposition rate of 600 angstrom/>Is then coated with alpha-NPD (NPB) to/>Deposition rate per second on the hole injection layer to form a semiconductor device having/> A hole transport layer of a thickness of (a).
Compound 3 (dopant) and CBP (host) were used as a base materialDeposition rate and/>Deposition rate per second is co-deposited on the hole transport layer to form a film having/>Is a layer of a thickness of the emissive layer.
BAlq toDeposition rate per second on the emissive layer to form a film having/>And depositing Alq 3 on the hole blocking layer to form a hole blocking layer having a thickness of/>Is deposited on the electron transport layer to form a layer having a thickness of/>Is then vacuum deposited on the electron injection layer to form a layer having a thickness of/>A second electrode (cathode) of a thickness of (a) thereby completing a cathode having ITO/m-MTDATA/> /α-NPD/>CBP+ Compound 3 (10%)/>/BAlq/>/Alq3 /LiF/>/Al/>The fabrication of the organic light emitting device of the structure of (a).
Examples 2 to 9 and comparative examples A to C
An organic light emitting device was manufactured in the same manner as in example 1, except that: in forming the emission layer, for use as a dopant, the corresponding compound shown in table 5 was used instead of compound 3.
Evaluation example 3: evaluation of characteristics of organic light-emitting device
The organic light emitting devices manufactured according to examples 1 to 9 and comparative examples a to C were evaluated for respective driving voltages, light emission quantum efficiencies, roll-off ratios, and lifetimes (T 95). The results are shown in Table 5. The evaluation was performed using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A), and the lifetime (T 95) (at 6000 nit) was evaluated by measuring the amount of time elapsed until the luminance was reduced to 95% of the initial luminance of 100%. In table 5, the lifetime (T 95) (at 6000 nit) is expressed as a relative value (%). The roll-off ratio is calculated by the following equation:
Equation 20
Roll-off ratio= {1- (efficiency (at 9,000 nits)/maximum luminous efficiency) } ×100%
TABLE 5
/>
From table 5, it was confirmed that the organic light emitting devices of examples 1 to 9 had excellent driving voltage characteristics, high light emission quantum efficiency, low roll-off ratio, and excellent lifetime characteristics, as compared with the organic light emitting devices of comparative examples a to C.
The organometallic compound according to the embodiment has excellent electrical characteristics and thermal stability. Accordingly, the organic light emitting device including the organometallic compound may have excellent driving voltage, quantum efficiency, power efficiency, color purity, and lifetime characteristics. Such an organometallic compound has excellent phosphorescent light-emitting characteristics, and thus, when used, can provide a diagnostic composition having high diagnostic efficiency.
It should be understood that the embodiments described herein should be considered in descriptive sense only and not for purposes of limitation. The descriptions of features or aspects in various embodiments should typically be considered as available for other similar features or aspects in other embodiments.
Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims.
Claims (16)
1. An organometallic compound represented by formula 1A:
1A
Wherein, in the formula 1A,
M is platinum (Pt),
X 1 is O or S, and the total number of the components is equal to or less than zero,
X 2 and X 4 are N,
X 3 is C, and the total number of the components is C,
The bond between X 1 and M and the bond between X 3 and M are covalent bonds, and the bond between X 2 and M and the bond between X 4 and M are coordination bonds,
Y 1 is C, and the total number of the components is C,
X 51 is N- [ (L 7)b7-(R7)c7 ],
L 1-L4 and L 7 are each independently selected from
Single bond, phenyl group, and naphthalene group; and
A phenyl group and a naphthalene group each substituted with at least one selected from the group consisting of: deuterium, C 1-C20 alkyl, and C 1-C20 alkyl substituted with at least one deuterium,
B1 to b4 and b7 are each independently 1,
R 1-R4 and R 7 are each independently selected from:
Hydrogen, deuterium-containing groups, C 1-C20 alkyl, and C 1-C20 alkoxy;
C 1-C20 alkyl and C 1-C20 alkoxy each substituted with at least one selected from the group consisting of: deuterium, -CD 3、-CD2H、-CDH2, and C 1-C10 alkyl;
Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenyl, and naphthyl; and
Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenyl, and naphthyl, each of which is substituted with at least one selected from the group consisting of: deuterium, -CD 3、-CD2H、-CDH2、C1-C20 alkyl, and C 1-C20 alkoxy,
C1 to c4 and c7 are each independently integers from 1 to 5,
Each Z 1-Z4 is independently deuterium or a deuterium containing group,
A1 to a4 and n1 to n4 are each independently an integer of 0 to 20,
Wherein the organometallic compound represented by formula 1A satisfies one of the conditions a), b), and c): a) R 7 is deuterium or a deuterium containing group; b) The sum of n1 to n4 is 1 or more; or c) R 7 is deuterium or a deuterium containing group and the sum of n1 to n4 is 1 or more, and
Wherein the deuterium containing group is a first group substituted with at least one deuterium atom and the first group is selected from C 1-C20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenyl, or naphthyl, each of which is unsubstituted or substituted with at least one selected from: -CD 3、-CD2H、-CDH2, and C 1-C20 alkyl.
2. The organometallic compound according to claim 1, wherein
R 1-R4 and R 7 are each independently selected from:
Hydrogen, deuterium-containing groups, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, zhong Guiji, tert-decyl, phenyl, biphenyl, and naphthyl; and
Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, zhong Guiji, tert-decyl, phenyl, biphenyl, and naphthyl each of which is substituted with at least one member selected from the group consisting of: deuterium, -CD 3、-CD2H、-CDH2、C1-C10 alkyl, and C 1-C10 alkoxy.
3. The organometallic compound according to claim 1, wherein
R 1-R4 and R 7 are each independently selected from hydrogen, a group represented by the formula 9-1 to 9-19, deuterium ,-CH3,-CD3,-CD2H,-CDH2,-CD2(CD3),-CD(CD3)2,-C(CD3)3,-CD2-C(CD3)3,-CD2-CD(CD3)2,-CD2-CD2(CD3),-CD(CD3)-C(CD3)3,-CD(CD3)-CD(CD3)2,-CD(CD3)-CD2(CD3),-C(CD3)2-C(CD3)3,-C(CD3)2-CD(CD3)2,-C(CD3)2-CD2(CD3),, a group represented by the formula 10-1, 10-2, 10-9, 10-10, 10-13 to 10-20, 10-49 to 10-65, 10-70 to 10-75, 10-81, 10-82, 10-162 to 10-182, 10-207 to 10-212, and 10-227 to 10-232, and a group represented by the formula 11-1 to 11-3, 11-5 to 11-20, 11-22, 11-24, 11-25, and 11-27 to 11-41, and
Z 1-Z4 is each independently selected from deuterium ,-CD3,-CD2H,-CDH2,-CD2(CD3),-CD(CD3)2,-C(CD3)3,-CD2-C(CD3)3,-CD2-CD(CD3)2,-CD2-CD2(CD3),-CD(CD3)-C(CD3)3,-CD(CD3)-CD(CD3)2,-CD(CD3)-CD2(CD3),-C(CD3)2-C(CD3)3,-C(CD3)2-CD(CD3)2,-C(CD3)2-CD2(CD3), and a group represented by one of formulas 9-14 to 9-19, 11-1 to 11-3, 11-5 to 11-20, 11-22, 11-24, 11-25, and 11-27 to 11-41:
Wherein, in formulas 9-1 to 9-19, 10-1, 10-2, 10-9, 10-10, 10-13 to 10-20, 10-49 to 10-65, 10-70 to 10-75, 10-81, 10-82, 10-162 to 10-182, 10-207 to 10-212, 10-227 to 10-232, 11-1 to 11-3, 11-5 to 11-20, 11-22, 11-24, 11-25, and 11-27 to 11-41, the binding site to the adjacent atom is represented, and Ph is phenyl.
4. The organometallic compound according to claim 1, wherein
The deuterium containing group is selected from -CD3、-CD2(CD3)、-CD(CD3)2、-C(CD3)3、-CD2-C(CD3)3、-CD2-CD(CD3)2、-CD2-CD2(CD3)、-CD(CD3)-C(CD3)3、-CD(CD3)-CD(CD3)2、-CD(CD3)-CD2(CD3)、-C(CD3)2-C(CD3)3、-C(CD3)2-CD(CD3)2、-C(CD3)2-CD2(CD3)、 and groups represented by one of formulas 11-1 to 11-3, 11-5 to 11-20, 11-22, 11-24, 11-25, and 11-27 to 11-41:
Wherein the x in formulae 11-1 to 11-3, 11-5 to 11-20, 11-22, 11-24, 11-25, and 11-27 to 11-41 represent binding sites to adjacent atoms.
5. The organometallic compound according to claim 1, wherein at least one of < condition a > to < condition D > is satisfied:
< condition A >
N1 is 1,2, 3 or 4;
< condition B >
R 7 is deuterium or a deuterium containing group;
< condition C >
N3 is 1, 2 or 3;
< condition D >
N4 is 1,2, 3 or 4.
6. The organometallic compound of claim 1 wherein L 1 is a single bond.
7. The organometallic compound of claim 1 wherein L 2 is a single bond.
8. The organometallic compound of claim 1 wherein L 3 is a single bond.
9. The organometallic compound of claim 1 wherein L 4 is a single bond.
10. The organometallic compound of claim 1 wherein L 7 is a phenyl group.
11. The organometallic compound according to claim 1, wherein
The organometallic compound is one of the following compounds 1 to 6, 10 to 414, 416, 418, 420, 422 to 529, and 531 to 666:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
12. an organic light emitting device comprising:
A first electrode;
a second electrode; and
An organic layer disposed between the first electrode and the second electrode,
Wherein the organic layer comprises an emissive layer and at least one organometallic compound as defined in any of claims 1-11.
13. The organic light-emitting device of claim 12, wherein
The first electrode is an anode and the second electrode is an anode,
The second electrode is a cathode electrode and,
The organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
The hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and
The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
14. The organic light-emitting device of claim 12, wherein
The organometallic compound is included in the emissive layer.
15. The organic light-emitting device of claim 14, wherein
The emissive layer further includes a host, and the amount of the host is greater than the amount of the organometallic compound.
16. A diagnostic composition comprising at least one organometallic compound according to any of claims 1-11.
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